FComEx: L-Citrulline (PC000170)

Record Information

Version

1.0

Creation date

2015-10-09 22:29:02 UTC

Update date

2017-01-19 02:36:15 UTC

FoodComEx ID

PC000170

FoodDB Record

FDB011841

Chemical Information

Name

L-Citrulline

Description

Occurs in the juice of watermelon (Citrullus vulgaris) A non-essential amino acid and a precursor of arginine. Citrulline supplements have been claimed to promote energy levels, stimulate the immune system and help detoxify ammonia (a cell toxin). L-citrulline is made from L-ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from L-arginine as a by-product of the reaction catalyzed by the enzyme NO synthase. L-citrulline, while being an amino acid, is not involved in protein synthesis and is not one of the amino acids coded for by DNA. Although citrulline cannot be incorporated in proteins during protein synthesis, several proteins are known to contain citrulline as an amino acid. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases (PADs), which convert the amino acid arginine into citrulline. Proteins that contain citrulline residues include myelin basic protein (MBP), fillagrin and several histone proteins.; Citrulline is an amino acid made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family (NOS; Citrulline is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family (NOS; EC 1.14.13.39). Arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with release of nitric oxide.; EC 1.14.13.39). Citrulline's name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.; EC 1.14.13.39). In this reaction arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with the release of nitric oxide.; The organic compound citrulline is an ?-amino acid. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated in 1930. It has the idealized formula H2NC(O)NH(CH2)3CH(NH2)CO2H. It is a key intermediate in the urea cycle, the pathway by which mammals excrete ammonia.; The rind of watermelon (Citrullus lanatus) is a good natural source of citrulline. L-Citrulline is found in many foods, some of which are mung bean, cucurbita (gourd), nectarine, and acorn.

CAS Number

372-75-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2S)-2-amino-5-(carbamoylamino)pentanoate	biospider
(2S)-2-amino-5-(carbamoylamino)pentanoic acid	biospider
(S)-2-amino-5-(aminocarbonyl)aminopentanoate	biospider
(S)-2-amino-5-(aminocarbonyl)aminopentanoic acid	biospider
(S)-2-Amino-5-ureidopentanoate	biospider
(S)-2-Amino-5-ureidopentanoic acid	biospider
2-Amino-5-uredovalerate	biospider
2-amino-5-Uredovaleric acid	HMDB
2-Amino-5-ureidovalerate	biospider
2-Amino-5-ureidovaleric acid	biospider
A-amino-d-ureidovalerate	biospider
A-amino-d-ureidovaleric acid	biospider
a-amino-delta-Ureidovalerate	Generator
a-amino-delta-Ureidovaleric acid	Generator
a-amino-δ-ureidovalerate	Generator
a-amino-δ-ureidovaleric acid	Generator
Alpha-amino-delta-ureidovalerate	biospider
Alpha-amino-delta-ureidovaleric acid	biospider
Alpha-amino-gamma-ureidovalerate	biospider
Alpha-amino-gamma-ureidovaleric acid	biospider
Amino-ureidovalerate	biospider
Amino-ureidovaleric acid	biospider
CIR	biospider
Cit	ChEBI
CITRULLINE	ChEBI
Citrulline, l-	biospider
Citrulline; L-form	db_source
Cytrulline	biospider
D-ureidonorvaline	biospider
Delta-ureidonorvaline	biospider
DL-Citrulline	HMDB
Gammaureidonorvaline	biospider
H-cit-oh	biospider
L-2-Amino-5-ureido-valerate	biospider
L-2-Amino-5-ureido-valeric acid	biospider
L-2-Amino-5-ureidovalerate	biospider
L-2-Amino-5-ureidovaleric acid	biospider
L-citrulline (DCF)	biospider
L-Cytrulline	HMDB
L-N5-carbamoyl-Ornithine	biospider
L(+)-2-Amino-5-ureidovalerate	biospider
L(+)-2-Amino-5-ureidovaleric acid	biospider
L(+)-citrulline	biospider
N-carbamylornithine	biospider
N()-Carbamylornithine	HMDB
N(5)-(Aminocarbonyl)-DL-ornithine	HMDB
N(5)-(aminocarbonyl)-L-ornithine	biospider
N(5)-carbamoyl-L-ornithine	biospider
N(delta)-carbamylornithine	biospider
N(δ)-carbamylornithine	Generator
N<SUP>5</SUP>-(aminocarbonyl)ornithine	biospider
N5-(Aminocarbonyl)-L-ornithine	biospider
N5-(aminocarbonyl)-Ornithine	biospider
N5-(Aminocarbonyl)ornithine	biospider
N5-Carbamoyl-L-ornithine	HMDB
N5-carbamoylornithine	biospider
N5-carbamylornithine	biospider
ND-carbamylornithine	biospider
Ndelta-carbamy-ornithine	biospider
Ndelta-carbamylornithine	biospider
Ngamma-carbamylornithine	biospider
Ornithine, N5-(aminocarbonyl)-	biospider
Ornithine, N5-carbamoyl-, L- (8CI)	biospider
Sitrulline	HMDB
Ureidonorvaline	biospider
Ureidovalerate	biospider
Ureidovaleric acid	biospider
α-amino-δ-ureidovalerate	Generator
α-amino-δ-ureidovaleric acid	Generator
δ-ureidonorvaline	Generator

Chemical Formula

C6H13N3O3

IUPAC name

(2S)-2-amino-5-(carbamoylamino)pentanoic acid

InChI Identifier

InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)

InChI Key

RHGKLRLOHDJJDR-UHFFFAOYSA-N

Isomeric SMILES

NC(CCCNC(O)=N)C(O)=O

Average Molecular Weight

175.1857

Monoisotopic Molecular Weight

175.095691297

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents